(S)-1-(4-{(3S,5R)-4-[2-((R)-1-Hydroxy-ethyl)-pyrimidin-4-yl]-3,5-dimethyl-piperazin-1-yl}-pyrimidin-2-yl)-ethanol

ID: ALA287890

Chembl Id: CHEMBL287890

PubChem CID: 9968745

Max Phase: Preclinical

Molecular Formula: C18H26N6O2

Molecular Weight: 358.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](O)c1nccc(N2C[C@@H](C)N(c3ccnc([C@@H](C)O)n3)[C@@H](C)C2)n1

Standard InChI:  InChI=1S/C18H26N6O2/c1-11-9-23(15-5-7-19-17(21-15)13(3)25)10-12(2)24(11)16-6-8-20-18(22-16)14(4)26/h5-8,11-14,25-26H,9-10H2,1-4H3/t11-,12+,13-,14+/m0/s1

Standard InChI Key:  ATNZXIACLONSSN-RFQIPJPRSA-N

Alternative Forms

1. Parent:

   

   ALA287890

   1-(4-{4-[2-(1-Hydroxy-ethyl)-pyrimidin-4-yl]-2,6-dimethyl-piperazin-1-yl}-pyrimidin-2-yl)-ethanol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.45

Molecular Weight (Monoisotopic): 358.2117

AlogP: 1.48

#Rotatable Bonds: 4

Polar Surface Area: 98.50

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.17

CX Basic pKa: 5.40

CX LogP: 2.69

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -0.56

References

1. Chu-Moyer MY, Ballinger WE, Beebe DA, Coutcher JB, Day WW, Li J, Oates PJ, Weekly RM..  (2002)  SAR and species/stereo-selective metabolism of the sorbitol dehydrogenase inhibitor, CP-470,711.,  12  (11): [PMID:12031323] [10.1016/s0960-894x(02)00208-1]

2. Mylari BL, Oates PJ, Zembrowski WJ, Beebe DA, Conn EL, Coutcher JB, O'Gorman MT, Linhares MC, Withbroe GJ..  (2002)  A sorbitol dehydrogenase inhibitor of exceptional in vivo potency with a long duration of action: 1-(R)-[4-[4-(4,6-dimethyl[1,3,5]triazin-2-yl)- 2R,6S-dimethylpiperazin-1-yl]pyrimidin-2- yl]ethanol.,  45  (20): [PMID:12238919] [10.1021/jm020288y]

Source

Source(1):

• Scientific Literature